For steaks I highly reccomend the Capitol Grille just off Michigan on St. Clair. I have tried most of the steak houses in Chicago, and the Capitol Grille is by far the best.
If you want to try a great Italian place that is a little off the beaten path, try Bella Notte around 1700 West Grand. Great food at great prices, and a lot of ambience. Much better for a quiet dinner than some of the better known Italian places.
Reservations recomended at both places.
Abe